Tetramethyl ammonium chloride supplier

Name
Tetramethylammonium chloride
EINECS 200-880-8
CAS No. 75-57-0
Article Data57
CAS DataBase
Density 1.17 g/cm³
Solubility >60 g/100 mL (20 °C ) in water
Melting Point >300 °C(lit.)
Formula C₄H₁₂NCl
Boiling Point 165.26°C (rough estimate)
Molecular Weight 109.599
Flash Point
Transport Information UN 2811 6.1/PG 2
Appearance white crystals
Safety 26-36/37-45-37/39-28A-28-36
Risk Codes 21-25-36/37/38-20/21/22
Molecular Structure
Hazard Symbols T, Xn
Synonyms Ammonium,tetramethyl-, chloride (8CI);Methanaminium, N,N,N-trimethyl-, chloride (9CI);Tetramethylammonium chloride (6CI);Tetramine chloride;
PSA 0.00000
LogP -2.67360

Synthetic route

: 75-59-2
tetramethyl ammoniumhydroxide

: 1605-65-8
N,N,N',N'-Tetramethylphosphorodiamidic chloride

A: 93048-79-4
tetramethylammonium bis(dimethylamino)phosphate

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In water for 3h;	A 99.5% B n/a

...Expand

: 593-81-7
trimethylamine hydrochloride

: 616-38-6
carbonic acid dimethyl ester

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;	99%
With 1-ethyl-3-methylimidazolium bromide at 169.84℃; for 8h;

: 616-38-6
carbonic acid dimethyl ester

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With ammonium chloride at 169.84℃; for 8h;	96%
With ammonium chloride at 169.84℃; for 8h;	96%

: 98-88-4
benzoyl chloride

: 63581-76-0
dimethyl-amidophosphoric acid monomethyl ester; tetramethylammonium salt

A: 75-57-0
tetramethlyammonium chloride

B: 106997-48-2
C10H14NO4P

Conditions

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;	A n/a B 93%

...Expand

: Hg((2-phenylazo)phenyl)2

: bis(tetramethylammonium) {TlCl5}

: tetramethylammonium trichloro(2-phenylazophenyl)thallate(III)

B: 2N(CH3)4(1+)*Hg2Cl6(2-)=[N(CH3)4]2[Hg2Cl6]

C: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In ethanol refluxing (6 h), solvent evapn. to dryness; residue recrystn. from dichloromethane/diethyl ether; elem. anal.;	A 85% B n/a C n/a

...Expand

: (Me4N)2{Mo3(μ3-S)(μ2-S2)3Cl6}

A: (PPh3)3Mo3(μ3-S)(μ2-S)3Cl4

B: 75-57-0
tetramethlyammonium chloride

C: 3878-45-3
triphenylphosphine sulfide

Conditions

Conditions	Yield
With P(C6H5)3 In methanol Stirring of a suspn. of Mo-compd. and PPh3 (MeOH, 1 h).; Filtn. of pptd. green solid, washing with hot MeOH and benzene, drying (vac.), elem. anal.;	A 82% B n/a C >99

...Expand

: Hg(2-dimethylaminomethylphenyl-C'N)2

: bis(tetramethylammonium) {TlCl5}

A: tetramethylammonium trichloro(2-dimethylaminomethylphenyl-C'N)thallate(III)

B: 2N(CH3)4(1+)*Hg2Cl6(2-)=[N(CH3)4]2[Hg2Cl6]

C: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In ethanol refluxing (6 h), solvent evapn. to dryness; residue recrystn. from dichloromethane/diethyl ether; elem. anal.;	A 77% B n/a C n/a

...Expand

: 31117-16-5
nido-B10H12CNMe3

: 7646-69-7
sodium hydride

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In tetrahydrofuran at 25°C;	60%

: (Me4N)2{Mo3(μ3-S)(μ2-S2)3Cl6}

A: Mo3(μ3-S)(μ2-S)3(dppe)3Cl4

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With C2H4(P2(C6H5)4) In methanol byproducts: (dppe)S2; Boiling of Mo-compd. with dppe (MeOH, 1 h).; Recrystn. of bright green ppt. from a CH2Cl2/hexane mixt., elem. anal.;	A 51% B n/a

: 74-87-3
methylene chloride

: 105334-48-3
Neopentyl N,N,N',N'-tetramethylphosphorodiamidite

A: 75-57-0
tetramethlyammonium chloride

B: Neopentyl N,N-dimethylphosphoramidochloridite

C: bisdimethylamino(methyl)neopentyloxyphosphonium chloride

Conditions

Conditions	Yield
Ambient temperature;	A 10.4% B 17 % Spectr. C 30.1%

...Expand

: 83095-83-4, 14647-25-7
[platinum(II)dichloride(1,2-bis(diphenylphosphino)ethane)]

: 12386-10-6
tetramethylammonium octahydrotriborate

A: (C2H5)3NB3H7

B: 1-{1,2-bis(diphenylphosphino-κP)ethane}-1-platina-arachno-tetraborane(7)

C: 1722-26-5
triethylamine-borane

D: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With triethylamine In acetonitrile under inert atm., 5 h stirring, pptn. of NMe4Cl, solvent removed in vacuo; chromy., eluating of by-products with hexane and main product with toluene;	A n/a B 25% C n/a D n/a

...Expand

: 88470-26-2
N,N-dimethoxyamine

: 75-50-3
trimethylamine

A: 593-81-7
trimethylamine hydrochloride

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With tert-butylhypochlorite In diethyl ether 1) -78 deg C, 0.5 h, 2) -8 deg C, 24 h;	A 15.7% B 22.8%

...Expand

: 12386-10-6
tetramethylammonium octahydrotriborate

: 65097-96-3
(1,4-bis(diphenylphosphanyl)butane)dichloridoplatinum(II)

A: (C2H5)3NB3H7

B: 1-{1,4-bis(diphenylphosphino-κP)butane}-1-platina-arachno-tetraborane(7)

C: 1722-26-5
triethylamine-borane

D: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With triethylamine In acetonitrile under inert atm., 5 h stirring, pptd. of NMe4Cl, solvent removed in vacuo; chromy., eluating of by-products with hexane, the main product with toluene;	A n/a B 20% C n/a D n/a

...Expand

: 59329-00-9
[1,3-bis(diphenylphosphino)propane]dichloroplatinum(II)

: 12386-10-6
tetramethylammonium octahydrotriborate

: 136813-66-6
cis-PtHCl(1,3-bis(diphenylphosphino)propane)

B: (dppp)PtB3H7

C: 136813-67-7
(PtH(dppp)2)Cl

: (Pt2H3((C6H5)2PCH2CH2CH2P(C6H5)2)2(1+))*Cl(1-)=(Pt2H3((C6H5)2PCH2CH2CH2P(C6H5)2)2)Cl

E: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With triethylamine In acetonitrile under inert atm., 5 h stirring, pptd. of NMe4Cl, solvent removed in vacuo, summarized yields of PtH(Cl)(dppp) and (PtH(dppp)2)Cl < 1%, further products; chromy., eluating of by-products with hexane, the main product with toluene, the (Pt2H3(dppp)2)Cl, PtH(Cl)(dppp) and (PtH(dppp)2)Cl with methanol, the PtH(Cl)(dppp) and (PtH(dppp)2)Cl were not isolated;	A n/a B 20% C n/a D 2% E n/a

...Expand

: 104413-90-3
[1,1'-bis(diphenylphosphino)ferrocene]platinum(II) chloride

: 12386-10-6
tetramethylammonium octahydrotriborate

A: (C2H5)3NB3H7

B: (((C6H5)2PC5H4)2Fe)PtB3H7

C: 1722-26-5
triethylamine-borane

: Pt2H3(((C6H5)2PC5H4)2Fe)2(1+)*Cl(1-)=Pt2H3(((C6H5)2PC5H4)2Fe)2Cl

E: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With triethylamine In acetonitrile under inert gas; stirring for 5 h;; evapn., washing, recrystn.;;	A n/a B 2% C n/a D 10% E n/a

...Expand

: 67-56-1
methanol

A: 75-57-0
tetramethlyammonium chloride

B: 75-50-3
trimethylamine

Conditions

Conditions	Yield
With ammonium chloride at 285℃;

: 6018-82-2
trimethylvinyl ammonium chloride

A: 5763-87-1
N,N-dimethylvinylamine

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
bei der trocknen Destillation im Stickstoffstrom;

: 74-87-3
methylene chloride

: 124-40-3
dimethyl amine

A: 506-59-2
N,N-dimethylammonium chloride

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
unter Druck;

...Expand

: 60-29-7
diethyl ether

: 98-09-9
benzenesulfonyl chloride

: 75-50-3
trimethylamine

A: 14417-01-7
N,N-dimethylbenzenesulfonamide

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
at 0℃;
at -80℃;

...Expand

: 98-09-9
benzenesulfonyl chloride

: 75-50-3
trimethylamine

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With diethyl ether at 0℃;

: 77-78-1
dimethyl sulfate

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With sodium hydroxide; ammonium chloride

: 74-87-3
methylene chloride

: 74-89-5
methylamine

A: 593-51-1
methylamine hydrochloride

B: 75-57-0
tetramethlyammonium chloride

...Expand

: 2344-80-1
Chloromethyltrimethylsilane

: 75-50-3
trimethylamine

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
at 210℃;

: 74-87-3
methylene chloride

: 75-50-3
trimethylamine

: 75-57-0
tetramethlyammonium chloride

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
With hydrogenchloride

: 13254-33-6
(3-carboxypropyl)trimethylammonium chloride methyl ester

A: 96-48-0
4-butanolide

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
at 0 - 250℃; Mechanism; Heating; pyrolysis of various carpronium chloride derivatives, labelled derivatives;

: 756-77-4
tetramethylammonium dimethyl phosphate

: 98-88-4
benzoyl chloride

A: 91489-49-5
benzoyl dimethyl phosphate

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;

...Expand

: 93048-79-4
tetramethylammonium bis(dimethylamino)phosphate

: 98-88-4
benzoyl chloride

A: 106997-52-8
benzoic acid-(tetramethyl-diamidophosphoric acid )-anhydride

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In acetonitrile for 3h; Ambient temperature; Title compound not separated from byproducts;

...Expand

: 98-88-4
benzoyl chloride

: 63581-76-0
dimethyl-amidophosphoric acid monomethyl ester; tetramethylammonium salt

A: 75-57-0
tetramethlyammonium chloride

B: 611-74-5
N,N-dimethylbenzamide

Conditions

Conditions	Yield
In acetonitrile for 4h; Heating;

...Expand

: 98-88-4
benzoyl chloride

: 91489-48-4
C4H12N(1+)*C4H9NO4P(1-)

A: 7449-76-5
N-acetyl-N-acetylbenzamide

B: 75-57-0
tetramethlyammonium chloride

Conditions

Conditions	Yield
In acetonitrile for 4h; Heating;

...Expand

: (2,11-(CH3)2-2,11-C2B9H9)2Ni

: 75-57-0
tetramethlyammonium chloride

: 12556-57-9
{N(CH3)4}{(1.2-C2B9H9(CH3)2)2Ni}

Conditions

Conditions	Yield
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%

: 33009-91-5
(7,8-(CH3)2-7,8-C2B9H9)Ni(2,11-(CH3)2-2,11-C2B9H9)

: 75-57-0
tetramethlyammonium chloride

: 12556-59-1
{N(CH3)4}{(1.2-C2B9H9(CH3)2)2Ni}

Conditions

Conditions	Yield
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%
With NaBH4 In ethanol redn. with 2-fold excess of NaBH4 in C2H5OH at room temp. (15 min), addn. of H2O, addn. of (N(CH3)4)Cl;; pptn.;;	100%

: hydrogen tetrachloroaurate(III) tetrahydrate

: 75-57-0
tetramethlyammonium chloride

: tetramethyl-ammonium; tetrachloroaurate (III)

Conditions

Conditions	Yield
In water under N2, light excluded; to aq. soln. of HAuCl4*4H2O (4.85 mmol) excess(Me4N)Cl added, stirred for 30 min; filtered, ppt. washed (H2O, EtOH, Et2O), vacuum-dried;	100%

: 75-57-0
tetramethlyammonium chloride

: nickel dichloride

: 2{N(CH3)4}(1+)*{NiCl4}(2-)={N(CH3)4}2{NiCl4}

Conditions

Conditions	Yield
In methanol under N2 or Ar; soln. of 3 equiv. of Me4NCl in MeOH heated to reflux; slurry of NiCl2 in MeOH added to boiling soln.; heated under reflux for 24h; filtered; solvent removed from filtrate under vac.;	99%
In ethanol 8:1 mixture; heating pptn. in i-pentanol;; pptn. washed with petroleum and dried at 60°C in vacuum;;
In ethanol 8:1 mixture; heating pptn. in i-pentanol;; pptn. washed with petroleum and dried at 60°C in vacuum;;
heating at 130-150°C for several hours; Evapn. of soln. of nitromethane in a vac. desiccator (CaSO4) yields to crystals.;

: 10025-99-7
potassium tetrachloroplatinate(II)

: 75-57-0
tetramethlyammonium chloride

: tetramethylammonium tetrachloroplatinate(II)

Conditions

Conditions	Yield
In water	99%

: 19624-22-7
pentaborane(9)

: 75-57-0
tetramethlyammonium chloride

: potassium hydride

: {(CH3)4N}(1+)*{B11H14}(1-)={(CH3)4N}{B11H14}

Conditions

Conditions	Yield
In 1,2-dimethoxyethane byproducts: H2, KCl; condensing 20.9mmol B5H9 into the vessel containing 8.88mmol KH and 9.17mmol ammonium salt at -196°C, warming to ambient temp., heating to 85°C for 2h, filtation;; removal of volatile material in high vac. (<10E-3 mm Hg), heating to 90°C for 24h in vac.; NMR:;	99%

...Expand

: (HNMe3)(7-SPh-8-Me-7,8-C2B9H10)

: 7789-20-0
water-d2

: 75-57-0
tetramethlyammonium chloride

: (NMe4)(10-D-7-SPh-8-Me-7,8-C2B9H9)

Conditions

Conditions	Yield
In tetrahydrofuran; water-d2 soln. Na2(7-SPh-8-Me-7,8-C2B9H9) in THF was prepared from (NHMe3)(7-SPh-8-Me-7,8-C2B9H10) (J.Am.Chem.So., 1968, V.90, P.862; P.879) and then treated with D2O and stirred under N2 for 15 min., THF was evapd. and Me4NCl in D2O was added; ppt. was filtered, washed with D2O and recrystd. from acetone/D2O; elem. anal.;	99%

...Expand

: 10170-68-0, 16997-54-9
trichlorotris(tetrahydrofuran)chromium(III)

: 142021-25-8
nitrido{bis-N,N'-(salicylaldehyde)ethylenediiminato}manganese(V)

: 7732-18-5
water

: 75-57-0
tetramethlyammonium chloride

: 75-05-8
acetonitrile

A: 105241-53-0
N,N'-ethylenebis(salicylideneiminato)manganese(III) chloride*acetonitrile

: [Cr(N)Cl4](2-)*2N(CH3)4(1+)*H2O=[N(CH3)4]2[Cr(N)Cl4]*H2O

Conditions

Conditions	Yield
In acetonitrile (N2); dissolving of CrCl3(THF)3 in CH3CN, addn. of Mn(N)(salen), stirring for 1 h, filtration, addn. of soln. of Me4NCl in CH3CN/C2H5OH/H2O (15:14:1) to filtrate; pptn., filtration, washing with CH3CN, drying, elem. anal.;	A 99% B 71%

...Expand

: Rh2(((C6H5)2PC2H4NCH3)2C6H4)(((C6H5)2PC2H4S)2C6H4)(2+)*2BF4(1-)=Rh2(((C6H5)2PC2H4NCH3)2C6H4)((C6H5)4P2C10H12S2)(BF4)2

: 201230-82-2
carbon monoxide

: 75-57-0
tetramethlyammonium chloride

: 827609-97-2
Rh2(((C6H5)2PC2H4NCH3)2C6H4)(((C6H5)2PC2H4S)2C6H4)(CO)2Cl2

Conditions

Conditions	Yield
In dichloromethane 1 atm. of CO, 2 equiv of (CH3)4NCl, CH2Cl2, room temp.;	99%

...Expand

: K[arachno-B9H14]

: 75-57-0
tetramethlyammonium chloride

: (CH3)4N(1+)*[B9H14](1-)=[(CH3)4N][B9H14]

Conditions

Conditions	Yield
In further solvent(s) all manipulations in vacuum line or under inert atm.; arachno-borane andMe4NCl placed in flask fitted with Solv-Seal adapter, evacuated, glyme condensed into system, warmed to room temp., stirred for 1 h; ppt. filtered off, solvent removed in vac.;	99%

: Rh2(((C6H5)2PC2H4S)2C6(CH3)4)(((C6H5)2PC2H4S)2C6H4)(2+)*2BF4(1-)=Rh2(((C6H5)2PC2H4S)2C6(CH3)4)((C6H5)4P2C10H12S2)(BF4)2

: 201230-82-2
carbon monoxide

: 75-57-0
tetramethlyammonium chloride

: 827609-96-1
Rh2(((C6H5)2PC2H4S)2C6(CH3)4)(((C6H5)2PC2H4S)2C6H4)(CO)2Cl2

Conditions

Conditions	Yield
In dichloromethane 1 atm. of CO, 2 equiv of (CH3)4NCl, CH2Cl2, room temp.;	99%

...Expand

: Rh2(((C6H5)2PC2H4O)2C14H8)(((C6H5)2PC2H4S)2C6H4)(2+)*2BF4(1-)=Rh2(((C6H5)2PC2H4O)2C14H8)((C6H5)4P2C10H12S2)(BF4)2

: 201230-82-2
carbon monoxide

: 75-57-0
tetramethlyammonium chloride

: 827609-98-3
Rh2(((C6H5)2PC2H4O)2C14H8)(((C6H5)2PC2H4S)2C6H4)(CO)2Cl2

Conditions

Conditions	Yield
In dichloromethane 1 atm. of CO, 2 equiv of (CH3)4NCl, CH2Cl2, room temp.;	99%

...Expand

: 12-(4-methoxypyridinium)-closo-1-monocarbadodecaborate

: 75-57-0
tetramethlyammonium chloride

: C6H15B11NO(1-)*C4H12N(1+)

Conditions

Conditions	Yield
Stage #1: 12-(4-methoxypyridinium)-closo-1-monocarbadodecaborate With lithium chloride In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere; Stage #2: tetramethlyammonium chloride for 2h; Inert atmosphere;	99%

: [(η5-4,7-Me2C9H5)Mo(CO)2(6,6'-dimethyl-2,2'-bipyridine)][BF4]

: 75-57-0
tetramethlyammonium chloride

: [(η3-4,7-Me2C9H5)Mo(CO)2(6,6'-dimethyl-2,2'-bipyridine)Cl]

Conditions

Conditions	Yield
In acetone for 48h; Inert atmosphere; Schlenk technique;	99%

: 75-57-0
tetramethlyammonium chloride

: 1838-41-1
tetramethylammonium dichloroiodate(I)

Conditions

Conditions	Yield
With hydrogenchloride; sodium hypochlorite; sodium iodide at 20℃; for 0.5h;	98%
With hydrogenchloride; dihydrogen peroxide; iodine In water; acetonitrile at 20℃; Cooling with ice;	97%
With hydrogenchloride; potassium iodate
With water
With Iodine monochloride; acetic acid

: 17526-08-8
1-methyl-2-methylthiolato-1,2-dicarba-closo-dodecaborane

: 75-57-0
tetramethlyammonium chloride

: tetramethylammonium 7-methyl-8-methylthiolato-S-7,8-dicarba-nido-undecaborate

Conditions

Conditions	Yield
With KOH In ethanol refluxing of the starting dicarbaborane and KOH in ethanol for 2 h under N2, eliminating of ethanol, dissolving of residue in water, addn. of Me4NCl; filtn., rechrystn. (EtOH-H2O), elem. anal.;	98%

: 17526-08-8
1-methyl-2-methylthiolato-1,2-dicarba-closo-dodecaborane

: 75-57-0
tetramethlyammonium chloride

: (SCH3)(CH3)C2B9H10(1-)*N(CH3)4(1+)

Conditions

Conditions	Yield
With KOH In ethanol KOH is added to flask contg. deoxygenated ethanol, stirred for 1 h, carborane is added, mixt. is refluxed for 2 h, solvent is evapd., water is added, filtn., N2 is bubbled through soln., NMe4Cl in water is added, pptn.; filtn., washing (water), recrystd. (ethanol/water); elem. anal.;	98%

: La2Na3(μ4-4-methylphenoxy)3(μ-4-methylphenoxy)6(THF)5

: 75-57-0
tetramethlyammonium chloride

: {Me4N}{La2Na2(μ4-4-methylphenoxy)(μ3-4-methylphenoxy)2(μ-4-methylphenoxy)4(4-methylphenoxy)2(THF)5}(THF)

Conditions

Conditions	Yield
In tetrahydrofuran (with exclusion of air and water) Me4NCl was added to a soln. of complex in THF, stirred for 24 h; centrifuged, evapd. to dryness; elem. anal.;	98%

: (HNMe3)(7-SPh-8-Ph-7,8-C2B9H10)

: 7789-20-0
water-d2

: 75-57-0
tetramethlyammonium chloride

: (NMe4)(10-D-7-SPh-8-Ph-7,8-C2B9H9)

Conditions

Conditions	Yield
In tetrahydrofuran; water-d2 soln. Na2(7-SPh-8-Ph-7,8-C2B9H9) in THF was prepared from (NHMe3)(7-SPh-8-Ph-7,8-C2B9H10) (J.Am.Chem.So., 1968, V.90, P.862; P.879) and then treated with D2O and stirred under N2 for 15 min., THF was evapd. and Me4NCl in D2O was added; ppt. was filtered, washed with D2O and recrystd. from acetone/D2O; elem. anal.;	98%

...Expand

: 13154-24-0
triisopropylsilyl chloride

: trimethylammonium 12-iodocarba-closo-dodecaborane

: 75-57-0
tetramethlyammonium chloride

: tetramethylammonium 1-triisopropylsilyl-12-iodocarba-closo-dodecaborane

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran byproducts: LiCl; n-butyllitium was added dropwise to a soln. of carborane in THF at 0°C, stirred for 30 min at room temp., cooled to 0°C, silyl-compound was added dropwise, stirred at room temp. for 3 h, the procedure was repeated; H2O was added, rotary evapd., H2O was added, (CH3)4NCl was added, ppt. was dried at 80°C overnight;	98%

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: 153984-80-6
1-(2-pyridyl)-1,2-dicarba-closo-dodecaborane(12)

: 75-57-0
tetramethlyammonium chloride

: 7-(2'-pyridyl)-7,8-nido-dicarbaundecaborate tetramethylammonium

Conditions

Conditions	Yield
With KOH In ethanol in Schlenk flask; soln. of KOH in EtOH was added to borate cluster, mixt. was refluxed for 3 h, cooled to room temp.; mixt. was evapd., residue was dissolved in water and treated with Me4NCl, solid was filtered off, washed with water and Et2O; elem. anal.;	98%

: 75-57-0
tetramethlyammonium chloride

: 70-70-2
4-hydroxypropiophenone

: 121-97-1
4-Methoxypropiophenone

Conditions

Conditions	Yield
With potassium carbonate In 1,2-dimethoxyethane at 145℃; for 0.416667h; Microwave irradiation; Inert atmosphere; Sealed vessel;	98%
With potassium carbonate at 150 - 160℃; for 4h;	81%

: 75-57-0
tetramethlyammonium chloride

: sodium 2-ethylhexanoic acid

: tetramethylammonium 2-ethylhexanoate

Conditions

Conditions	Yield
In water at 40℃; Flow reactor;	98%

: 12354-84-6, 12354-85-7
bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]

: C20H20FeN3OS(1+)*BF4(1-)

: 75-57-0
tetramethlyammonium chloride

: C30H34Cl2FeIrN3OS

Conditions

Conditions	Yield
Stage #1: C20H20FeN3OS(1+)*BF4(1-); tetramethlyammonium chloride With silver(l) oxide In dichloromethane; acetonitrile Molecular sieve; Inert atmosphere; Schlenk technique; Darkness; Stage #2: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; Schlenk technique;	98%

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: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer

: C20H20FeN3OS(1+)*BF4(1-)

: 75-57-0
tetramethlyammonium chloride

: C30H34Cl2FeN3ORhS

Conditions

Conditions	Yield
Stage #1: C20H20FeN3OS(1+)*BF4(1-); tetramethlyammonium chloride With silver(l) oxide In dichloromethane; acetonitrile Molecular sieve; Inert atmosphere; Schlenk technique; Darkness; Stage #2: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In dichloromethane at 20℃; Molecular sieve; Inert atmosphere; Schlenk technique;	98%

...Expand

: 930-69-8
sodium thiophenolate

: 75-57-0
tetramethlyammonium chloride

: 100-68-5
methyl-phenyl-thioether

Conditions

Conditions	Yield
In methanol at 65℃; for 10h;	97.2%

: 16872-09-6
1,2-dicarba-closo-dodecaborane(12)

: 75-57-0
tetramethlyammonium chloride

: [N(CH3)4][7,10-C2B10H13]

Conditions

Conditions	Yield
With 1,1-Dibromoethane; magnesium; iodine In tetrahydrofuran to suspn. Mg, I2, and dibromoethane in THF at 0°C soln. o-carborane in THF was added, left at room temp. for 30 min and refluxed for 9 h,mixt. was evapd. to dryness in vacuo, water was added, soln. was filter ed, excess aq. Me4NCl was added; solid was washed with water and Et2O;	97%

: 71-23-8
propan-1-ol

: 75-57-0
tetramethlyammonium chloride

: 61470-34-6
β-n-butoxycarbonylethyltin trichloride

: 78192-82-2
(CH3)4N(1+)*C3H7OCOCH2CH2SnCl4(1-)

Conditions

Conditions	Yield
In methanol; propan-1-ol 1). BuOCOC2H4SnCl3, excess refluxing n-propanol for 4 h; 2). 1 mol Me4NCl in MeOH was added;; solvent was removed; elem. anal.;;	97%

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Tetramethyl ammonium chloride Consensus Reports

Reported in EPA TSCA Inventory.

Tetramethyl ammonium chloride Specification

Tetramethyl ammonium chloride, with CAS number of 75-57-0, can be called methanaminium, N,N,N-trimethyl-, chloride (1:1); N,N,N-Trimethylmethanaminium chloride; TMAC. The chemical formula (CH3)4N+Cl- is often abbreviated further as Me4N+Cl-. It is a white crystal. It is a very hygroscopic colourless solid that is soluble in water and polar organic solvents.

Preparation of Tetramethyl ammonium chloride: Tetramethylammonium chloride can be synthesized by the alkylation of ammonium chloride with dimethyl carbonate, in the presence of 1-ethyl-3-methyl imidazolium bromide ([EMIM]+Br-) as an ionic liquid catalyst. The overall reaction is:
NH4+Cl- + 2 (CH₃O)₂CO → N(CH₃)₄+Cl- + 2 H₂O + 2 CO₂

Uses of Tetramethyl ammonium chloride: Tetramethyl ammonium chloride (CAS NO.75-57-0) is used as a phase transfer catalyst for anionic reactants. In small concentrations, also has been shown to enhance yield 5-10 fold at 3M by stabilizing the AT base pairs. Besidea used with polymerase chain reactions to increase yield and specificity.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing and gloves;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Wear suitable gloves and eye/face protection;
5. After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H12N.ClH/c1-5(2,3)4;/h1-4H3;1H/q+1;/p-1;
(2)InChIKey=OKIZCWYLBDKLSU-UHFFFAOYSA-M;
(3)Smiles[N+](C)(C)(C)C.[ClH-];

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
frog	LDLo	subcutaneous	2gm/kg (2000mg/kg)	PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) CARDIAC: OTHER CHANGES	Skandinavisches Archiv fuer Physiologie. Vol. 10, Pg. 201, 1900.
guinea pig	LDLo	unreported	20mg/kg (20mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 7, Pg. 183, 1900.
mouse	LD50	intraperitoneal	10mg/kg (10mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	National Technical Information Service. Vol. OTS0536975,
mouse	LD50	subcutaneous	40mg/kg (40mg/kg)		National Technical Information Service. Vol. ORNL-5576,
mouse	LDLo	oral	125mg/kg (125mg/kg)		Journal of Pharmaceutical Sciences. Vol. 69, Pg. 327, 1980.
mouse	LDLo	unreported	20mg/kg (20mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 7, Pg. 183, 1900.
rabbit	LDLo	subcutaneous	6mg/kg (6mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 7, Pg. 183, 1900.
rat	LD50	intraperitoneal	10mg/kg (10mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: REGIONAL OR GENERAL ARTERIOLAR OR VENOUS DILATION LUNGS, THORAX, OR RESPIRATION: CYANOSIS	National Technical Information Service. Vol. OTS0536975,
rat	LD50	oral	50mg/kg (50mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	National Technical Information Service. Vol. OTS0536975,

Product Name

Tetramethylammonium chloride

Synthetic route

Tetramethyl ammonium chloride Consensus Reports

Tetramethyl ammonium chloride Specification

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